HCID 58958458, compound → HCID 58958453, compound

HRID 915170Notes

Reaction equation

HRID 915170 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[S:11][C:10](/[N:12]=C/N(C)C)=[N:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1>[NH4+].[OH-]>[NH2:12][C:10]1[S:11][C:7]([C:5]([NH:4][CH:1]2[CH2:2][CH2:3]2)=[O:6])=[CH:8][N:9]=1

Participants

3

Reactant 1

HCID 58958458HCID 58958458, compound

Product 1

HCID 58958453HCID 58958453, compound

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

N-cyclopropyl-2-{[(1E)-(dimethylamino)methylidene]amino}-1,3-thiazole-5-carboxamide 23-3 (1.01 g, 4.23 mmol) was heated to 75° C. in 20 mL of concentrated NH4OH in a sealed tube. After 4 hours the hydrolysis was complete and most of the liquid was evaporated off. Additional water was then added and the pH adjusted to 6. The aqueous layer was extracted with ethyl acetate (4×) and all organics were combined, dried, evaporated and flushed with toluene (2×). 1H-NMR (DMSO): 8.06 ppm (s, 1H); 7.55 ppm (s, 1H); 7.42 ppm (s, 2H); 2.68 ppm (m, 1H); 0.64 ppm (m, 2H); 0.48 ppm (m, 2H).

Workup

  1. customwas evaporated off
  2. additionAdditional water was then added
  3. extractionThe aqueous layer was extracted with ethyl acetate (4×)
  4. customdried
  5. customevaporated
  6. customflushed with toluene (2×)

Sources & evidence

ORD record
ord-6669bdc7c32841579f4d32dac3c5f5f3
Source dataset
uspto-grants-2007_09
Patent number
US07265134B2

Reaction notes

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